Guo Na, Liu Jiang, Qin Long, Jiang Du, You Xing, Lu Kui, Teng Yu-Ou, Yu Peng
a Key Laboratory of Industrial Microbiology, Ministry of Education, College of Biotechnology, Tianjin University of Science and Technology , Tianjin 300457 , China.
J Asian Nat Prod Res. 2015;17(4):377-83. doi: 10.1080/10286020.2014.1003048. Epub 2015 Jan 28.
A natural xanthone, 1,3,6-trihydroxy-5-methoxyxanthone, was totally synthesized for the first time by six steps in 31% overall yield. The xanthone skeleton was formed by a one-step synthesis in 80% yield, and five of its novel derivatives were also obtained by this approach. This synthetic strategy and all the derivatives could be further used for the preparation of other natural xanthones. All the xanthones were characterized by NMR and ESI-MS, and the cytotoxicity of these xanthones was evaluated against HepG2 and HT-29 cells, and the preliminary structure-activity relationship was evaluated from the results. It was proved that the presence of 3-OH group in the molecule is crucial for its biological activity, while the presence of substituents at C-5 and C-6 may also be beneficial.
首次通过六步反应以31%的总收率全合成了天然呫吨酮1,3,6-三羟基-5-甲氧基呫吨酮。呫吨酮骨架通过一步反应合成，收率为80%，并且还通过该方法获得了其五种新型衍生物。这种合成策略以及所有衍生物可进一步用于制备其他天然呫吨酮。所有呫吨酮均通过核磁共振（NMR）和电喷雾电离质谱（ESI-MS）进行表征，并评估了这些呫吨酮对肝癌细胞（HepG2）和人结肠癌细胞（HT-29）的细胞毒性，并根据结果评估了初步的构效关系。结果表明，分子中3-羟基（3-OH）基团的存在对其生物活性至关重要，而C-5和C-6位取代基的存在可能也有益处。
